Magnesium Carbonate → 2-{3-[3-(2-Ethyl-5-hydroxy-4-thiazol-4-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acid

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A mixture of 2-(3-{3-[5-benzyloxy-4-(2-chloroacetyl)-2-ethylphenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester (500 mg, 0.792 mmol), thioformamide (20 mL, 8.0 mmol), and magnesium carbonate in dioxane (10 mL) was heated at reflux for 2 h. The mixture was cooled to room temperature and diluted with diethyl ether and 0.2 M sodium hydroxide solution. The organic layer was separated, washed with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 10% ethyl acetate/90% hexane) of the residue provided 254 mg (50%) of the title compound as a colorless oil. 1H NMR (CDCl3) δ 8.91 (s, 1H), 8.11 (s, 1H), 7.87 (dd, J=8, 1 Hz, 1H), 7.84 (d, J=1 Hz, 1H), 7.40 (m, 6H), 7.08 (m, 2H), 6.80 (d, J=8 Hz, 1H), 6.68 (d, J=8 Hz, 1H), 6.62 (s, 1H), 6.43 (d, J=8 Hz, 1H), 5.16 (s, 2H), 4.21 (t, J=6 Hz, 4H), 3.83 (s, 3H), 2.68 (m, 4H), 2.32 (quintet, J=6 Hz, 2H), 1.56 (hextet, J=8 Hz, 2H), 1.21 Ct, J=7 Hz, 3H), 0.90 (t, J=7 Hz, 3H); TOF MS ES+ exact mass calculated for C38H40NO6S (p+1): m/z=638.2576. Found: 638.2579. IR (CHCl3, cm−1) 2964, 1719, 1563, 1461.

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